Picolinic acid → 5-Chloro-3-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)-1,2-dihydropyridin-2-amine

HRID 1622662Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1622662
Br[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].N1C=CC=CC=1C(O)=O.[NH2:29][C:30]1[C:35]([C:36]2[CH:41]=[CH:40][C:39]([OH:42])=[CH:38][CH:37]=2)=[CH:34][C:33]([Cl:43])=[CH:32][N:31]=1.[NH4+].[Cl-]>CS(C)=O.[Cu]I>[Cl:43][C:33]1[CH:34]=[C:35]([C:36]2[CH:41]=[CH:40][C:39]([O:42][C:2]3[CH:7]=[CH:6][N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[CH:3]=3)=[CH:38][CH:37]=2)[CH:30]([NH2:29])[NH:31][CH:32]=1

Komponenten

8

Edukt 5

HCID 1018Picolinic acidHCID 25517Ammonium ChlorideHCID 62657Potassium Phosphate, TribasicHCID 234369504-Bromo-2-(trifluoromethyl)pyridineHCID 667480044-(2-Amino-5-chloropyridin-3-yl)phenol

Produkt 1

HCID 682809385-Chloro-3-(4-{[2-(trifluoromethyl)pyridin-4-yl]oxy}phenyl)-1,2-dihydropyridin-2-amineAusbeute 55,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

A mixture of 4-bromo-2-(trifluoromethyl)pyridine (282 mg), tripotassium phosphate (481 mg), picolinic acid (27.9 mg), copper (I) iodide (21.58 mg) and 4-(2-amino-5-chloropyridin-3-yl)phenol (250 mg) in DMSO (5 ml) was stirred at 140° C. under N2 overnight. The mixture was poured into sat. NH4Cl aq. and extracted with EtOAc. The organic layer was separated, washed with brine, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane) to give the title compound (230 mg) as a pale yellow solid.

Aufarbeitung

  1. extractionextracted with EtOAc
  2. customThe organic layer was separated
  3. washwashed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by column chromatography (NH silica gel, eluted with EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-067e0a9814b044838e012b7ac5b46074
Quelldatensatz
uspto-grants-2014_07
Patentnummer
US08778934B2

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